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Cheap flights from Chicago Midway Airport to San José from $157

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 1/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:42 pm - 1:52 pmMDW-SJO
17h 10m1 stop
Multiple Airlines Logo
12:39 pm - 8:46 amSJO-MDW
20h 07m2 stops
$298Multiple Airlines
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Fri, Dec 5 - Tue, Dec 9
Multiple Airlines Logo
3:52 pm - 11:25 amMDW-SJO
19h 33m2 stops
Multiple Airlines Logo
12:33 pm - 8:45 pmSJO-MDW
8h 12m1 stop
$306Multiple Airlines
Find Deal
Mon, Jan 12 - Fri, Jan 16
Multiple Airlines Logo
8:42 pm - 12:25 pmMDW-SJO
39h 43m2 stops
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
$313Multiple Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Multiple Airlines Logo
8:42 pm - 1:52 pmMDW-SJO
17h 10m1 stop
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
$316Multiple Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Frontier Logo
6:00 am - 1:43 pmMDW-SJO
7h 43m1 stop
Frontier Logo
2:58 pm - 11:26 pmSJO-MDW
8h 28m1 stop
$384Frontier
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Mon, Jan 12 - Sat, Jan 17
Delta Logo
12:48 pm - 10:15 pmMDW-SJO
9h 27m1 stop
Delta Logo
2:31 pm - 10:26 pmSJO-MDW
7h 55m1 stop
$410Delta
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Thu, Jan 29 - Tue, Feb 3
Delta Logo
9:34 am - 10:15 pmMDW-SJO
12h 41m2 stops
Delta Logo
7:00 am - 3:40 pmSJO-MDW
8h 40m1 stop
$414Delta
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Fri, Jan 30 - Sat, Feb 7
Southwest Logo
6:15 am - 7:30 pmMDW-SJO
13h 15m1 stop
Southwest Logo
9:40 am - 10:55 pmSJO-MDW
13h 15m1 stop
$421Southwest
Find Deal
Tue, Feb 3 - Tue, Feb 10
Southwest Logo
5:00 am - 12:50 pmMDW-SJO
7h 50m1 stop
Southwest Logo
9:40 am - 8:40 pmSJO-MDW
11h 00m2 stops
$426Southwest
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Tue, Jan 27 - Tue, Feb 3
Frontier Logo
6:00 am - 1:43 pmMDW-SJO
7h 43m1 stop
Frontier Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
$478Frontier
Find Deal
Sat, Jan 10 - Sat, Feb 21

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Jan 29
MDW12:48 pmChicago Midway
9h 27m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 3
SJO2:31 pmSan José Juan Santamaria Intl
7h 55m
1 stop
MDW10:26 pmChicago Midway
$410
Find similar
Delta
Jan 30
MDW9:34 amChicago Midway
12h 41m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
Feb 7
SJO7:00 amSan José Juan Santamaria Intl
8h 40m
1 stop
MDW3:40 pmChicago Midway
$414
Find similar
Delta
Nov 13
MDW10:47 amChicago Midway
11h 20m
1 stop
SJO10:07 pmSan José Juan Santamaria Intl
Nov 17
SJO2:31 pmSan José Juan Santamaria Intl
9h 09m
1 stop
MDW11:40 pmChicago Midway
$476
Find similar

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Feb 3
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Feb 10
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$421
Find similar
Southwest
Jan 27
MDW5:00 amChicago Midway
7h 50m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Feb 3
SJO9:40 amSan José Juan Santamaria Intl
11h 00m
2 stops
MDW8:40 pmChicago Midway
$426
Find similar
Southwest
Dec 10
MDW10:15 amChicago Midway
10h 15m
1 stop
SJO8:30 pmSan José Juan Santamaria Intl
Dec 13
SJO2:15 pmSan José Juan Santamaria Intl
8h 20m
1 stop
MDW10:35 pmChicago Midway
$449
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 10, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 12/5

8:42 pm-1:52 pm

1 stop17h 10m

San José Juan Santamaria Intl

Tue 12/9

12:39 pm-8:46 am

2 stops20h 07m

$298

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 1/12

3:52 pm-11:25 am

2 stops19h 33m

San José Juan Santamaria Intl

Fri 1/16

12:33 pm-8:45 pm

1 stop8h 12m

$306

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 12/5

8:42 pm-12:25 pm

2 stops39h 43m

San José Juan Santamaria Intl

Thu 12/11

12:39 pm-9:58 pm

1 stop9h 19m

$313

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 12/5

8:42 pm-1:52 pm

1 stop17h 10m

San José Juan Santamaria Intl

Thu 12/11

12:39 pm-9:58 pm

1 stop9h 19m

$316

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 1/12

6:00 am-1:43 pm

1 stop7h 43m

San José Juan Santamaria Intl

Sat 1/17

2:58 pm-11:26 pm

1 stop8h 28m

$384

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 1/29

12:48 pm-10:15 pm

1 stop9h 27m

San José Juan Santamaria Intl

Tue 2/3

2:31 pm-10:26 pm

1 stop7h 55m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 1/30

9:34 am-10:15 pm

2 stops12h 41m

San José Juan Santamaria Intl

Sat 2/7

7:00 am-3:40 pm

1 stop8h 40m

$414

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/3

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Tue 2/10

9:40 am-10:55 pm

1 stop13h 15m

$421

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 1/27

5:00 am-12:50 pm

1 stop7h 50m

San José Juan Santamaria Intl

Tue 2/3

9:40 am-8:40 pm

2 stops11h 00m

$426

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 1/10

6:00 am-1:43 pm

1 stop7h 43m

San José Juan Santamaria Intl

Sat 2/21

2:58 pm-11:25 pm

1 stop8h 27m

$478

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $542. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $770. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the evening. Our users have found flights to San José in the evening for as low as $453. Flights in the morning are often more expensive with an average ticket price of $736.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Direct flights

None
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
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  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 7h 25m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,235 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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